Prologue

“You’re new here, aren’t you?” Those were his first words to me. (His last, twenty-five years later, would be “I’m sorry.”) Already he had turned the tables on me. After all, I was the reporter. The one who was supposed to be asking the questions.

I had been warned about the unique challenges of interviewing Steve Jobs. The night before, over beers, my new colleagues at the San Francisco bureau of the Wall Street Journal had told me to bring a flak jacket to this first meeting. One of them said, only half jokingly, that interviewing Jobs was often more combat than questioning. It was April 1986, and Jobs was already a Journal legend. Bureau lore had it that he had dressed down another Journal reporter by posing this straightforward question: “Do you understand anything at all, anything at all about what we’re discussing?”

I’d had plenty of experience with real flak jackets during my years reporting in Central America in the early 1980s. I’d spent much of that time in El Salvador and Nicaragua, where I’d interviewed everyone from truck drivers motoring through war zones, to American military advisers in the jungle, to Contra commandantes in their hideouts, to presidents in their palaces. On other assignments I’d met with obstreperous billionaires like T. Boone Pickens and H. Ross Perot and Li Ka-shing, with Nobel Prize winners like Jack Kilby, with rock stars and movie idols, renegade polygamists, and even the grandmothers of would-be assassins. I wasn’t easily intimidated. Yet for the full twenty-minute drive from my home in San Mateo, California, to the headquarters of NeXT Computer in Palo Alto, I brooded and fretted about how best to interview Jobs.

Part of my unease came from the fact that, for the first time in my experience as a journalist, I would be calling on a prominent business leader who was younger than I. I was thirty-two years old; Jobs was thirty-one and already a global celebrity, hailed, along with Bill Gates, for having invented the personal computer industry. Long before Internet mania started churning out wunderkinds of the week, Jobs was technology’s original superstar, the real deal with an astounding, substantial record. The circuit boards he and Steve Wozniak had assembled in a garage in Los Altos had spawned a billion-dollar company. The personal computer seemed to have unlimited potential, and as the cofounder of Apple Computer, Steve Jobs had been the face of all those possibilities. But then, in September of 1985, he had resigned under pressure, shortly after telling the company’s board of directors that he was courting some key Apple employees to join him in a new venture to build computer “workstations.” The fascinated media had thoroughly dissected his departure, with both Fortune and Newsweek putting the ignominious saga on their covers.

In the six months since, the details of his new startup had been kept hush-hush, in part because Apple had filed lawsuits trying to prevent Jobs from hiring away its employees. But Apple had finally dropped those suits. And now, according to the publicist from Jobs’s PR agency who called my boss at the Journal, Steve was willing to do a handful of interviews with major business publications. He was ready to start the public fan-dance that would begin to reveal in detail what exactly NeXT was up to. I was thoroughly fascinated, and equally wary; I didn’t want to get taken in by the notoriously charismatic Mr. Jobs.

THE DRIVE SOUTH to Palo Alto is a trip through the history of Silicon Valley. From Route 92 in San Mateo over to Interstate 280, a “bucolic” eight-laner skirting San Andreas Lake and Crystal Springs Reservoir, which store drinking water for San Francisco piped in from the Sierras; past the blandly ostentatious venture-capitalist habitat along Sand Hill Road in Menlo Park and traversing the oblique, mile-long Stanford Linear Accelerator, which slashes like a hairline fracture through the landscape and beneath the freeway; past the “Stanford Dish” radio telescope, and the white-faced Herefords and ornate oak trees dotting the expansive greenbelt behind the university campus. The winter and spring rains had resurrected the prairie grass on the hills, turning them briefly as green as a golf course from their usual dull yellow, and peppering them with patches of orange, purple, and yellow wildflowers. I was so new to the Bay Area that I didn’t yet realize that this was the most beautiful time of year to make this drive.

My exit—Page Mill Road—was the home street address of Hewlett-Packard, early biotech pioneer ALZA Corporation, Silicon Valley “facilitators” like Andersen Consulting (now called Accenture), and the law firm Wilson Sonsini Goodrich & Rosati. But first you hit the university-owned Stanford Research Park, with its groves of low-slung corporate research-and-development labs situated with lots of grassy elbow room. Xerox’s famed Palo Alto Research Center (PARC), where Steve first saw a computer with a mouse and a graphical “bitmapped” screen interface, resides here. This was where he had chosen to headquarter NeXT.

A young woman from NeXT’s PR firm, Allison Thomas Associates, escorted me through the boxy, two-story, concrete-and-glass office building to a small conference room with a view of a half-filled parking lot and not much more. Steve was waiting there. He greeted me with a nod, dismissed the flack, and, before I could get seated, popped that first question.

I wasn’t sure if Steve wanted a monosyllabic answer, or if he was genuinely curious about who I was and where I came from. I assumed the latter, so I started ticking off the places and industries I’d written about for the Journal. Right after leaving graduate school at the University of Kansas, I’d moved to Dallas for the paper, where I’d written about aviation, airlines, and electronics, since Texas Instruments and Radio Shack were based there. Along the way I had won some notoriety for a profile of John Hinckley, the privileged son of a Texas oilman who shot President Reagan in 1981.

“What year did you graduate from high school?” he interjected. “Nineteen seventy-two,” I replied, “and I spent seven years in college but never quite got my master’s degree.” “That’s when I graduated from high school,” he interjected. “So we’re about the same age.” (I found out later that he had skipped a grade.)

I then explained that I’d spent two years each in Central America and Hong Kong writing and reporting on geopolitical issues for the Journal, and a year in Los Angeles, before finally wangling my dream job in San Francisco. At this point, it really was beginning to feel like a job interview. Except that Jobs wasn’t reacting much to any of my answers.

“So do you know anything about computers?” he asked, interrupting again. “Nobody who writes for the major national publications knows shit about computers,” he added, shaking his head with a practiced air of condescension. “The last person who wrote about me for the Wall Street Journal didn’t even know the difference between machine memory and a floppy!”

Now I felt on somewhat firmer footing. “Well, I was an English major, formally, but I programmed some simple games and designed relational databases on a mainframe in college.” He rolled his eyes. “For a couple of years, I worked nights as a computer operator processing the daily transactions for four banks on an NCR minicomputer.” He was staring out the window now. “And I bought an IBM PC the very first day they were available. At Businessland. In Dallas. Its serial number started out with eight zeroes. And I installed CP/M first. I only installed MS-DOS when I sold it before we moved to Hong Kong, because that’s what the buyer wanted.”

At the mention of those early operating systems and a competitor’s product he perked up. “Why didn’t you get an Apple II?” he asked.

Good question, but seriously … why was I letting this guy interview me?

“I never had one,” I allowed, “but now that I’m here, I got the Journal to buy me a Fat Mac.” I had convinced the big guys in New York that if I was going to be writing about Apple, I’d better be familiar with their latest machines. “I’ve been using it for a couple of weeks. So far, I do like it better than a PC.”

I had picked the lock. “Wait till you see what we’re going to build here,” he told me. “You’ll want to get rid of your Fat Mac.” We’d finally reached the point of the interview, the destination Steve had wanted all along—the place where he could tell me how he was going to outdo the company he had founded, and best the people, most notably Apple CEO John Sculley, who had effectively banished him from that kingdom.

Now he would take my questions, although he didn’t always respond to them directly. I was curious, for example, about his eerily empty headquarters. Were they really going to assemble computers here? It sure didn’t look like manufacturing space. Was he bankrolling the whole thing, or was he lining up some investors? He’d sold all his Apple shares save one, netting him about $70 million, but that wasn’t enough to fund a company this ambitious. At times he veered off into completely unexpected terrain. As we talked, he drank steaming hot water from a pint beer glass. He explained that when he ran out of tea one day, it dawned on him that he liked plain old hot water, too. “It’s soothing in the very same way,” he said. Eventually he would steer the conversation back to his main pitch: higher education needed better computers, and only NeXT could deliver them. The company was working closely with both Stanford and Carnegie Mellon—universities with highly respected computer science departments. “They’ll be our first customers.”

Despite his evasiveness and his determination to hew to a single message, Jobs was a vivid presence. The intensity of his self-confidence made me hang on his every word. He spoke in carefully constructed sentences, even when trying to answer an unexpected question. Twenty-five years later, at his memorial service, Steve’s widow, Laurene, testified to the “fully formed aesthetic” he possessed from a very young age. That confidence in his own judgment and taste came through in his answers. It also came through in the fact, as I realized over the course of our conversation, that he really was interviewing me, testing me to see if I “grokked”—understood—what was special about what he had done and what he planned to do at NeXT. Later, I came to realize that this was because Steve wanted whatever was written about him and his work to measure up to his own high standard of quality. At this stage of his life, he thought he could probably do anybody’s job better than they could—it was an attitude that gnawed at his employees, of course.

The interview lasted forty-five minutes. The plans he laid out for NeXT were sketchy; as it turned out, this was an early sign of the troubles the company would experience over the years. There was, however, one tangible thing he did want to discuss: the NeXT logo. He gave me a fancy brochure explaining the creative evolution of the snazzy corporate symbol Paul Rand had designed. The booklet itself had been designed by Rand personally, with expensive translucent leaves separating thick, creamy pages embossed with a step-by-step guide to how he had settled upon an image that spoke in “multiple visual languages.” The logo was a simple cube with NeXT spelled out in “vermillion against cerise and green, and yellow against black (the most intense color contrast possible),” and “poised at a twenty-eight degree angle,” according to the pamphlet. At that time, Rand was noteworthy as one of America’s leading graphic designers; he was famous for dreaming up the visual identities of IBM, ABC Television, UPS, and Westinghouse, among others. For this pamphlet, and for a single, take-it-or-leave-it draft of a corporate logo, Jobs had happily parted with $100,000 of his money. That extravagance, albeit in the pursuit of perfection, was a quality that would not serve him well at NeXT.

I DID NOT write a story after that first meeting. A fancy logo for an infant company didn’t qualify as news, no matter who had commissioned it, no matter who had designed it. (Besides, back then the Wall Street Journal never published photographs; in fact, it never printed anything in color. So even if I had wanted to write about Steve’s shiny new bauble, its subtle and impractical beauty would have been doubly lost on the Journal ’s readers, who cared little for design at the time.)

Not writing a feature was the first salvo in the twenty-five-yearlong negotiation that marked our relationship. As with most journalist/source relationships, there was one main reason Steve and I wanted to connect: we each had something the other needed. I could deliver the front page of the Wall Street Journal and, later, the cover of Fortune magazine; he had a story that my readers wanted, and that I wanted to tell better and earlier than any other journalist. He usually wanted me to write about a new product of his; my readers wanted to know about him as much as the product—if not more. He wanted to point out all the glories of the product and the genius and beauty of its creation; I wanted to get behind the scenes, and to cover the competitive ups and downs of his company. This was the subtext of most of our interactions: a transaction in which we each hoped to cajole the other into some sort of advantageous deal. With Steve, this could be like a card game where one day I’d feel we were partners playing bridge and the next I’d feel like a sucker holding eight-high in poker. More often than not, he made me feel like he had the edge—whether or not that was true.

Despite the fact that the Journal didn’t publish anything at the time, Steve told Cathy Cook, a Silicon Valley vet then working for Allison Thomas, that the interview went fine and that he thought I was “okay.” From time to time, he would have Cathy invite me over to NeXT for updates. There wasn’t much worth covering, frankly, at least in the eyes of the Journal —I didn’t write my first big piece about NeXT until 1988, when Steve finally unveiled the company’s first computer workstation. But the visits were always intriguing and invigorating.

One time he called me in to crow about persuading Ross Perot to invest $20 million in NeXT. On the face of it, they were the oddest couple: Perot, the crew-cut, buttoned-down, uber-patriotic, navy veteran bankrolling a former hippie who still preferred to go barefoot, was a vegetarian, and didn’t believe in using deodorant. And yet I now knew Steve well enough to understand that he and Perot, whom I’d interviewed a few times, were actually kindred spirits: both were idiosyncratic, idealistic autodidacts. I told him that he absolutely had to visit Perot in his office at Electronic Data Systems (EDS) in Dallas, if for no other reason than to see his over-the-top collection of histrionic eagle sculptures and the colonnade of U.S. flags lining the headquarters driveway. Steve laughed, and rolled his eyes in amusement: “Been there, done that.” He asked if I thought he was crazy for liking Perot. “How could anyone not like Perot at least a little after meeting him?” I replied. “He’s funny. ” Steve cackled in agreement, and then added, “Seriously, I think there’s a lot I can learn from him.”

Over time, our similar ages became a bridge more than a barrier. Steve and I had navigated similar adolescent rites of passage. I could say the same thing about Bill Gates, whom I also covered extensively, but he wasn’t the product of a working-class upbringing or public schools as Steve and I were. All three of us had dodged the bullet of serving in Vietnam because the military draft was abolished by the time we had turned eighteen. Yet Steve and I, more than Bill, were true products of the antiwar, peace and love, tune in/turn on generation. We were music nuts and gaga for gadgets, and we weren’t afraid to experiment with outlandish new ideas or experiences. Steve had been adopted as a child, and we did occasionally talk about what that had been like, but that aspect of his upbringing never seemed nearly as big an influence on his intellectual and cultural development as was the larger social and political milieu—and the high-tech sandbox—in which we came of age.

In those early years, Steve had an important reason to cultivate our relationship. In the ever-shifting computer world of the late 1980s, building breathless anticipation for his Next Big Thing was crucial to attracting potential customers and investors, and Steve would need plenty of the latter, given that NeXT would take nearly five years to produce a working computer. Throughout his life, Steve had a keen sense of the tactical value of press coverage; this was just one part of what Regis McKenna, perhaps his most important early mentor, calls “Steve’s natural gift for marketing. Even when he was twenty-two years old he had the intuition,” McKenna elaborated. “He understood what was great about Sony, about Intel. He wanted that kind of image for what he was going to create.”

Knowing that Apple was also among the companies I covered for the Journal, and later for Fortune, Steve would call up at seemingly random moments over the coming years to offer me “intelligence” that he’d heard from former colleagues who were still there, or simply to share his opinions on the interminable executive soap opera at his old company in Cupertino. Over time I learned that he was a reliable source about the mess that Apple became in the early 1990s—and I also came to realize that there was nothing random about those calls. Steve always had an ulterior motive: sometimes he was hoping to glean something about a competitor; sometimes he had a product he wanted me to check out; sometimes he wanted to chastise me for something I’d written. In the latter case, he could also play the withholding game; once, in the late 1990s, after his return to the company he had cofounded, I sent him a note to say that I thought it was about time for me to write another Apple story for Fortune. I had been out of touch for several months because I’d had open-heart surgery—he had called me at the hospital to wish me well—but now I was ready to jump on another piece. His email reply was simple: “Brent,” he wrote, “as I recall, you wrote a rather mean story about me and Apple last summer. I remember this hurting my feelings. Why did you write such a nasty story?” But a few months later he relented, and cooperated for another cover feature about the company.

Ours was a long, complicated, and mostly rewarding relationship. When I would run into Steve at industry events, he would introduce me as his friend, which was flattering, odd, true, and yet not true all at the same time. During the brief time when he had an office in Palo Alto near Fortune ’s bureau, I would run into him around town now and then, and we’d stop to chat about all kinds of things. Once, I helped him shop for his wife Laurene’s birthday present. I visited his home many times, always for one work reason or another, but with an informality that I’ve never encountered from another CEO. And yet there was never a minute where the basic terms of our relationship weren’t clear: I was the reporter, he was the source and subject. He enjoyed some of my stories—others, like the one that prompted that email, infuriated him. My independence and his hoarding of information created the borders of our relationship.

This necessary distance expanded during the last few years of his life. Both of us got very sick in the mid-2000s; he was first diagnosed with pancreatic cancer in 2003, while in 2005 I contracted endocarditis and meningitis during a trip to Central America, which put me in a near coma for fourteen days and eventually took away almost all my hearing. He knew more about my illness than I knew about his, of course. Still, he did sometimes reveal details—one time we even compared surgical scars, much like Quint (Robert Shaw) and Hooper (Richard Dreyfuss) in the movie Jaws. He visited me in the Stanford hospital twice during the weeks when I was recovering—stopping by when coming in for regular checkups with his oncologist. He told me some awful jokes about Bill Gates, and excoriated me for having continued to smoke cigarettes despite his admonitions over the years. Steve always did love to tell people how to conduct their personal lives.

AFTER STEVE DIED, reams of armchair analysis unfurled: articles, books, movies, and television shows. Often they resurrected old myths about Steve, using stereotypes that had been created way back in the 1980s, when the press discovered the wunderkind from Cupertino. In those early years, Steve was susceptible to the flattery of the press, and he opened himself and his company to reporters. He was at his most undisciplined and most intemperate then. As much as he showed a genius for imagining breakthrough products, he also could display a disturbing meanness and indifference toward both employees and friends. So when he started limiting access, and cooperating with the press only when he needed to promote his products, the tales from those early days at Apple became the conventional wisdom about his personality and thinking. Perhaps that’s why the posthumous coverage reflected these stereotypes: Steve was a genius with a flair for design, a shaman whose storytelling power could generate something magical and maleficent called a “reality distortion field”; he was a pompous jerk who disregarded everyone else in his single-minded pursuit of perfection; he thought he was smarter than anyone else, never listened to advice, and was an unchanging half-genius, half-asshole from birth.

None of this jibed with my experience of Steve, who always seemed more complex, more human, more sentimental, and even more intelligent than the man I read about elsewhere. A few months after his death, I started combing through the old notes, tapes, and files from my stories about him. There were all kinds of things I’d forgotten: off-the-cuff notes I’d written about him, stories he’d told me during interviews that I couldn’t use at the time for one sensitive reason or another, old chains of emails we’d exchanged, even a few tapes I’d never transcribed. There was an audiocassette he’d made for me that was a dubbed copy of one given to him by John Lennon’s widow, Yoko Ono, with all the various versions of “Strawberry Fields Forever” recorded during its lengthy composition process. These were all stored away in my garage, and unearthing them triggered many buried memories of Steve over the years. After rustling through these personal relics from the past for a few weeks, I decided that it wasn’t enough to grumble about the one-dimensional myths about Steve that were ossifying in the public mind; I wanted to offer a fuller picture and deeper understanding of the man I had covered so intensely, in a way that hadn’t been possible when he was alive. Covering Steve had been fascinating and dramatic. His was a truly Shakespearean tale, full of arrogance, intrigue, and pride, of perceived villains and ham-handed fools, of outrageous luck, good intentions, and unimagined consequences. There were so many ups and so many downs in so short a time that it had been impossible to draw the broad trajectory of his success while he was living. Now I wanted to take the long view of the man I’d covered for so many years, the man who had called himself my friend.

THE MOST BASIC question about Steve’s career is this: How could the man who had been such an inconsistent, inconsiderate, rash, and wrongheaded businessman that he was exiled from the company he founded become the venerated CEO who revived Apple and created a whole new set of culture-defining products that transformed the company into the most valuable and admired enterprise on earth and that changed the everyday lives of billions of people from all different socioeconomic strata and cultures? The answer wasn’t something Steve had ever been all that interested in discussing. While he was an introspective guy, he was not inclined to retrospection: “What’s the point in looking back,” he told me in one email. “I’d rather look forward to all the good things to come.”

A real answer would have to show how he changed, who influenced those changes, and how he applied what he’d learned to the business of making great computing devices. As I pored over my old documents, I kept coming back to the time that many have described as his “wilderness” years, the dozen years between his first tenure at Apple and his return. That era, from 1985 to 1997, is easy to overlook. The lows aren’t as dramatic as the blowups of his first tenure at Apple, and the highs, of course, aren’t as thrilling as those he engineered in the first decade of the twenty-first century. These were muddled, complicated times, and not the stuff of easy headlines. But those years are in fact the critical ones of his career. That’s when he learned most everything that made his later success possible, and that’s when he started to temper and channel his behavior. To overlook those years is to fall into the trap of only celebrating success. We can learn as much, if not more, from failure, from promising paths that turn into dead ends. The vision, understanding, patience, and wisdom that informed Steve’s last decade were forged in the trials of these intervening years. The failures, stinging reversals, miscommunications, bad judgment calls, emphases on wrong values—the whole Pandora’s box of immaturity—were necessary prerequisites to the clarity, moderation, reflection, and steadiness he would display in later years.

By the end of that decade in the woods, despite his many missteps, Steve had, remarkably enough, salvaged both NeXT and Pixar. The legacy of the first secured his professional future, while the triumph of the second ensured his financial well-being. His experience at both companies taught him lessons that, in retrospect, determined the future of Apple and helped define the world we live in. Steve could be intransigent, and nothing was ever learned easily or superficially, but learn he did. Driven and curious even when things were tough, he was a learning machine during these years, and he took to heart all that he gleaned.

No one works in a vacuum. Getting married and beginning a family changed Steve profoundly, in ways that had an enormous positive impact on his work. I had plenty of glimpses into Steve’s personal life over the years, and several encounters with Laurene and their children. But I was not a close friend of the family. When I started to report this book, in late 2012, it seemed that I might not learn much more about his personal life. Saddened by his death and feeling burned by some of what had been published about Steve posthumously, many of his closest colleagues and friends originally refused to talk to me. But that changed over time, and those conversations with his most intimate friends and colleagues—including the only four Apple employees to attend his private burial—revealed a side of Steve that I had sensed, but had not fully understood, and that I have certainly never read about elsewhere. Steve was capable of extraordinary compartmentalization. It’s a talent that allowed him to master and keep track of the various pieces of an entity as complex as Apple upon his return. It allowed him to maintain his focus despite the cacophony of worries that came with knowing he had cancer. It also allowed him to maintain a deep and meaningful life outside the office, while revealing little of that to people who weren’t part of his close inner circle.

Of course, he could be a difficult man, even late in his life. For some people, he was hellish to work for. His belief in the value of his mission allowed him to rationalize behavior that many of us might well deplore. But he could also be a loyal friend, and an encouraging mentor. He was capable of great kindness and genuine compassion, and he was an attentive and loving father. He believed deeply in the value of what he chose to do with his life, and he hoped those close to him believed in the value of their work just as deeply. For a man who so thoroughly “deviated from the mean,” as his friend and colleague Ed Catmull, the president of Pixar, puts it, he had deeply human feelings, strengths, and failings.

What I have always loved about business journalism, and what I have learned from the very best colleagues I’ve worked with, is that there is always a human side to the seemingly calculated world of industry. I knew this was true about Steve when he was alive—no one else I have ever covered was so passionate about the creations of his business. But only in writing this book have I come to understand just how much the personal life and the business life of Steve Jobs overlapped, and just how much the one informed the other. You can’t really understand how Steve became our generation’s Edison and Ford and Disney and Elvis, all rolled into one, until you understand this. It’s what makes his reinvention such a great tale.

AT THE END of our first interview, Steve walked me down the neat and glimmering hallways of NeXT’s headquarters to the exit. We didn’t exchange small talk. As far as he was concerned, our conversation was over. As I exited he didn’t even say goodbye. He just stood there, looking out the glass doors toward the entrance of the parking lot on Deer Creek Road where a crew of workmen was installing a 3-D version of the NeXT logo. As I drove away, he was lingering there still, staring at his hundred-grand logo. He knew in his bones, as he would say, that he was about to do something great. In reality, of course, he had no idea what was ahead of him.